50 Questions to ask a guy to get to know him

By on November 14, 2015

When you are in the beginning stages of a relationship it is not only fun, but important that you try to gain insight into who and what he really is. These questions may give you a clue not only about how he feels for you, but also if a future together is possible.


1. Do you mind if I don’t want to cuddle afterwards?

Most guys are not in the business of “cuddling”. By asking him if he doesn’t mind that you don’t want to cuddle you will let him know that you understand that it may not be his “thing” and it will put him at ease.

2. Do you think you could teach me something without getting irritated?

A woman will often ask too many questions during instruction. How much patience will he have for you?

dress to impressed

3. Are you a jeans or mini-skirt lover?

The guy who is more of a mini-skirt lover is probably going to expect you to put a little more effort into your appearance when with him.


4. Do you like to talk or would you rather sit back and listen?

Most guys are not talkers. It is said that the average woman says about 2000 words a day. The average guy says about 500.  Some guys talk a lot during the dating phase and then don’t say a word for years at a time.

5. If you could be anyone who would it be?

Everyone has someone that they admire, or that wish they were more like. Sometimes it can also tell you what his motivations are and if he is really himself, or trying to be someone else.

6. Would you rather give up your car or your television?

This is like asking are you a go-getter or a couch potato.

7. Would it bother you if my ex-boyfriend was in prison for violence?

This will also show his courageous side. It will tell you if he doesn’t mind coming to your defense and if he will play the protector when need be.

8. Are there any chick flicks that you actually enjoyed?

If he admits to liking something like The Notebook, you know that there is some sentiment in there.

9. What movie did you see that you liked but wouldn’t admit it to anyone?

We all have things we do when no one else is watching. Those are the things that really define who we are. Who is he deep down inside?


10. How long before you would give a girl the keys to your apartment?

This is an indication of how long he has to be with someone before he lets her into his world.

11. Would you rather be a tiger or a bear?

A tiger is more stealth, a bear is more brute strength. Does he do things through reasoning, or does he just go in and force his way. The answer to this question may give you the answer.

12. Would you date a girl who wanted ten children?

This isn’t really about wanting 10 children it is about respecting someone’s wants and being able to negotiate them.

listening music

13. Would you respect me if I listened to disco?

Is he someone who doesn’t care about the silly side of you?

14. Would you still think I was attractive if I lost my hair?

This will tell you if he is an unconditional love believer. When you are with someone for the long term you want to ensure that it really is in good times and bad.

15. If I got fat would you still love me?

You want someone who is going to love you for your insides, not only for what you look like on the outside. On the other hand, you want someone who pushes you to always be your best. If you allow yourself to get fat and he does and says nothing, then he may not be the best person to bring out the best in you.

16. Should I wear tight clothes or comfortable ones?

This will answer the question whether he cares more about himself or you. Of course he is probably going to like you in clothes that show off your assets, but he knows that comfy ones are better for you. This can give you insight into who is number one in his mind.

17. Would you be alright if I didn’t like to talk so much?

In general, talk too much. By asking him if it is okay to not talk so much you are communicating that you are okay with not having to fill the silence with chit chat all the time.


18. Vacation in Colorado or Cancun?

He is an adventurous and spontaneous soul, or is he a beach bum. This will tell you what he wants to do with his leisure time.

19. How do you keep your figure so thin?

By turning the tables back at him it also tells him that you aren’t that into yourself. Guys like a girl who can keep their figure, but not one that is so self-absorbed all they care about is the way that they look instead of who they are.

20. Do you ever find other guys attractive?

Is he okay with his feminine side? Many guys hide who they are and always put up a tough guy front. There is no way that a guy never finds another guy attractive.


21. What is a deal breaker in a relationship for you?

How set in his convictions is he that an issue would be a deal breaker?

22. If I told you I legally couldn’t be within 60 feet from a Grammar School would you worry?

This is just a funny question to make him think. Just make sure that after you ask you tell him you were just kidding!

23. Will you always tell me the truth even if I don’t want to hear it?

You want to find someone who will always bring out the best in you. You don’t want someone to tell you one thing and think another.

24. Would you rather spend a Saturday with me or watching a sports game?

Does he like to hang out with the guys, or is he alright giving you his time. It is okay if he likes to watch a sports game on the weekends, but ideally what he will answer is that he would like to do both. That will tell you that he wants to include you into his world.


25. Pizza or steak?

Italian stallion or carnivore?

26. Is personality really that important if someone is beautiful?

Will he love you when you get old and wrinkly or find a hot young mistress.

27. Would you rather be happy or rich?

Happiness is found in relationships, rich is found in objects. Does he want you or does he want things?

love 1

28. Do you believe in soul mates?

Are you just another date, or could you be the one he is supposed to pair with for the rest of his life?

29. Is there such a thing as happily ever after?

Does he believe that things can be perfect or is he more of a pessimist?

30. Do you ever dream about your wedding day?

How sentimental is he? If he hasn’t you can bet that he won’t ever remember your anniversary and probably not your birthday.

31. Does your mother like your taste in women?

How much does he value his mother’s opinion? A guy who never brings home the same type of girl as his mother likes, doesn’t care that much about her opinion.


32. Is family important to you?

How important will a family with you be with him? If he isn’t close to his own family that may indicate that he has some secrets in his past, or that he isn’t much of a bonder.

33. Do you want to coach little league someday?

Does he want kids and if he does, is he going to be the type of dad that is involved in their lives?

James Tupper

34. Workaholic or just because you have to?

If he doesn’t like his job you may encounter some real problems when he hits midlife. The last thing you want is someone who is going to go through a major midlife crisis.

35. Climb a mountain or the corporate ladder?

Is he going to take the time to explore while you are young or is he going to be tied to a board room? You can’t have memories never made. Where are his priorities going to be?

36. Strong hand parenting or soft touch?

Is he old school, or more lax. Parenting can be one of the biggest things that breaks up even the best marriages.

37. Do you curse?

Is he just being polite because you don’t know him very well, or is he a gentleman through and through?

dress on a budget

38. Do you want a girl who is ready in 15 minutes, or someone who takes time to do it up?

Is he going to expect you to always look perfect, or will he love you just the way you are?

39. Do you secretly look at other girls when on a date?

What does he think about commitment. Does it mean just when you are together, or even when you are apart?

40. What is your favorite perfume and why?

Does he like prepubescent scents, or more mature smells. The worst case scenario he likes what his mom wears.


41. Do you still think about your first love?

How hard does he fall when he does fall? Most guys will never forget their first love, but some will not admit to it. How much does he trust you to tell the truth.

42. Who was your first crush and why did you adore her?

Often your first crush is your ideal girl. What type of characteristics did she have?


43. Do you like to get there fast or enjoy the ride?

Is he always in a rush or does he take the time to look around him. Some guys are so focused that they miss out on most of life.

44. Do you like foreplay or is it for your partner?

This will tell you what your future sex life will be. Guys stop doing the things they are only doing for you when the relationship gets comfortable.

45. What is your five year plan?

Are you in it? Is marriage in it? Are kids in it?

his family

46. If your mom wasn’t nice to your wife would you stick up for her?

Will he stick with his wife in any situation, even if she may not always be right?

47. Momma’s boy or Daddy’s guy?

Are you going to have problems with his mom? Most momma’s boys never stop seeking the approval of their moms, even to the disadvantage of their wife.

48. What music do you listen to when no one else is listening?

What secretly gets his groove on? Is he silly or kind of funky?

49. When you were little what did you want to be?

Many of us forget our dreams as we get older. Ask what he wanted to be and if that is not what he is, find out why.

50. Do you learn from your mistakes and not do it again or try it differently?

Is he willing to get hurt and still try again? It is okay to try something again when you have a negative outcome, you just have to try doing it in a different way.

A fun way to pass the time, asking these silly questions may get you some serious answers about whether he is the right guy for you. For a lifetime of bliss, getting the messy discussions out of the way up front is an excellent idea!

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